(Or, am I over thinking everything)
There is a girl (Jen) that I've been acquaintances with for about 3-4 years. I recently asked her if she would be okay with me getting to know her better. In my mind, this puts the scenario at me having an interest in her, but perhaps not the other way around (though she is willing to at least consider me).
This brings me to the crux of my issue, anything I can think of doing from here out seems very artificial. A casual lunch/dinner is an easy one, and so is a movie (though I'm told these are actually bad ideas). But after that, I just can't wrap my head around how I can make the random date ideas (that the internet seems to think are good) more natural. They make sense if there is a mutual interest, people are happy to do anything with the person they like, but without that interest "Hey, wanna go.... people watching/to a cooking class/do some other random activity that is completely out of left field with me?" seems like a very good way to bore Jen.
I figure that until Jen has an active interest in me (refer to bolded statement), the interactions should at least be non-awkward and be interesting enough to let her have an enjoyable time. So my question is, how can I make these intentional one-on-ones seems more natural?
(To be clear, I'm not asking "what should I do", but "how should I do it")